


Then You Just Might

by J (jaywright)



Category: Critical Role (Web Series)
Genre: Caleb Widogast Deserves Nice Things, Dresses, M/M
Language: English
Status: Completed
Published: 2020-07-20
Updated: 2020-07-20
Packaged: 2021-03-04 20:42:23
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,765
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25392556
Author URL: https://archiveofourown.org/users/jaywright/pseuds/J
Summary: “Anyway, I’m sorry if I made you uncomfortable.”“You didn’t. You...you made me comfortable.”
Relationships: Caduceus Clay/Caleb Widogast
Comments: 9
Kudos: 167





	Then You Just Might

**Author's Note:**

> kink meme fill for Caleb in a Dress prompt: https://criticalkink.dreamwidth.org/3194.html?thread=1195898#cmt1195898

“Anyone else can borrow a dress too, if you like!” Jester said brightly as Beau inspected herself in the mirror, tugging at the hem of the red dress as if she could magically lengthen it if she pulled hard enough.

“Here, this one would look good on you, Caduceus,” she continued, pulling out a pale green robe and draping it over his shoulder. “And Fjord, look, this one’s the color of the sea – “ Fjord’s hands fumbled at catching a blue dress as it sailed out of the wardrobe at him. “Oh! Caleb!” She spun around with a dark green dress in her hands and held it up to him. “This would look _so good_ on you.”

His hands came up to catch the dress almost automatically as she whirled away, chattering about _probably_ still having something small enough that it might fit Nott, and her voice faded into the background as he looked down at the fabric, felt it soft against his fingers. He lifted his eyes to the mirror, seeing his own reflection behind Beau, and quickly let the dress drop, folding it carefully over his arm.

“Oh, this is nice, Jester,” Caduceus was saying, and Caleb looked up to find him turning slowly, the dress hanging loosely around him, sash undone like a gentle flowing coat. “Thanks!” he said earnestly.

Fjord reached to hang the one he was holding back up in the wardrobe. “Yeah, thanks, Jester,” he said. “It’s a good color, but it’s not really my style.”

Her enthusiasm deflated a little as she said, “Oh, okay, I guess – “ but she interrupted herself with a huge grin as Nott stepped out from behind a screen in the corner of the room. She was in Veth form, her eyes wide as she looked down at herself, and she did a little twirl, the purple dress a little too long, but flaring out delightfully as she spun.

“Oh,” Caleb said. Her eyes flickered up to meet his almost hesitantly. “It looks…” he didn’t have the words for it, for the expression of hesitant almost-joy on Veth’s face as she let herself feel pretty for the first time in a very long time. “Good,” he finally settled on.

“Good!” Jester repeated, smacking him on the arm as she swept past him to primp at Veth’s hair, adjust the sleeves a little for her. “She looks _amazing_. Yeza’s going to _fall over_ when he sees you. Come on.” She took Veth’s hand and started dragging her toward the door. “Let’s go find him right now.” 

Beau and Fjord followed, Beau’s shoulders shifting uncomfortably against the straps of the dress, and Caduceus paused in front of the mirror to perform a little swoop with the robe.

“I’m just…” Caleb said, and hefted his pack in the direction of the rooms they’d been given. Caduceus looked up at him, and if Caleb hadn’t been traveling with him for so long, he might have missed the way his eyes flickered perceptively down at the dress hastily curled up with his other belongings. Caleb felt his face go hot, and he nearly pushed past Caduceus to shove the dress back into the wardrobe, but then Caduceus turned back to the mirror, admiring himself some more. 

“It’s nice,” he said mildly. “Wearing something that makes you feel…” his eyes met Caleb’s in the mirror. “Well, feel anything, really.” He nodded toward the door. “Go handle your stuff. We’ll wait.”

Caleb nodded wordlessly, and shuffled off toward the furthest room. He tossed his pack onto the bed and laid the dress out flat beside it, letting his fingers linger for just a moment too long against the soft fabric. He imagined how it would feel against his skin, the sweep of it over his legs as he moved. Then he pictured Jester’s face lighting up as she saw him, the slight eyebrow raise from Fjord, the complicated mix of emotions that would cross Beau’s face before it settled on a smirk, and Veth…whose relationship to appearances was so changing and fragile, and who desperately didn't need anyone outshining her at this moment.

He resolutely didn’t think about what he would see on Caduceus’s face. Instead, he whirled out of the room before he could have another thought about it.

It was late when they made it back to the Chateau, leaving Veth with her family, and even later when he stood abruptly from the table where they were gathered, Beau and Fjord staring challengingly at each other over a hand of cards, Jester blatantly peering over Fjord’s shoulder and making unsubtle signals to Beau. Caduceus was sprawled out beside them, half watching, a lazy smile on his face, and his eyes flickered up to Caleb as he stood.

“Turning in?” he asked, and Caleb nodded.

“I have some work to do. A spell I’d like to copy. And it has been a bit of a long day.”

“A few of them,” Caduceus agreed. “They only had two rooms available, so I’ll be up in a while. Leave a spot for me in your alarm, would you?”

“Always do,” Caleb said gruffly. “It is never set against any of you.”

“I know,” Caduceus said. He nodded at Beau and Fjord. “I’ve gotta see what happens here, though. So I’ll be a while.”

Caleb felt like there was meaning laced into the words that he didn’t want to acknowledge, so he just nodded abruptly, said a quick good night to the others, and hurried up to the room. 

Caduceus had indeed placed his pack beside the other bed, and Caleb summoned Frumpkin before he set Alarm, letting him pace the room and sniff at the surroundings that were almost becoming familiar. When Caleb turned back around from the door, Frumpkin had settled down directly on top of the dress, looking up at him.

“Well?” Caleb asked him. “What do you think?” Frumpkin looked up at him, then down at the dress. He gave it a careful sniff, turned in three circles, and settled down comfortably on it. Caleb chuckled wryly. “You’re no help,” he said. Frumpkin blinked lazily at him. “All right,” Caleb said, “shoo. You’re not invited for this,” and he crossed the room, opening the door and gesturing out of it. Frumpkin stood, stretching luxuriously, and trotted out to settle down in the hall outside the room.

Alone in the room, Caleb took some time removing his pack from the bed, arranging it on the floor, settling the pillows, but his eyes kept drifting back to the dress. He knew Caduceus had given him the gift of time, and he was squandering it with his indecisiveness, but his mind kept coming back to the sight of himself behind Beau in the mirror in Jester’s room, his eyes hesitant, the green of the dress soft and unfamiliarly lovely against his skin.

He swallowed, closed his eyes, and cursed under his breath, then started to undress.

His breath was unsteady as he pulled the dress down over his head, gliding effortlessly down over his skin. His fingers fumbled against the fastenings, but when he turned to the mirror in the corner, he looked…perfect.

Jester had been right. The color was right for him, and the cut was flattering, the fabric flexible enough to accommodate Jester’s ample bosom, but not looking strangely bunchy or loose around his flat chest. Instead, the neckline framed his collarbone, the small sleeves curved gently over his shoulders, and the skirt…he shifted his hips a little, and the skirt flared enticingly around his legs. He couldn’t take his eyes off himself. It was still Caleb in the mirror, disheveled and in need of a shave, but he looked – he _felt_ , and his mind went back to Caduceus’s words about wearing something that made you _feel_ – unfamiliarly attractive.

He didn’t know how long he stood there, staring at himself, and eventually letting his hands tentatively slip over his body, shivering at the sensation of his hands through the fabric, closing his eyes, almost able to imagine that they belonged to someone else –

A cold wash of panic flooded over him as he felt Frumpkin reach out, sending him the image of Caduceus loping down the hall. Caleb was scrambling for the bed, for his clothes, when he felt Frumpkin’s thought – the image of Caduceus leaning down to ruffle him between the ears and say softly, gently, “Hey there, buddy. Would he be alright with me going in there right now, you think?”

Caleb’s immediate reaction was _No_ , a flare of panic and desperation as he grabbed the hem of the dress, prepared to tear it from his body, but then he paused, thinking of Caduceus swaying in a dress in front of the mirror himself, of the utterly neutral expression he’d had when he eyed Caleb taking the dress with him, of the gentle way he’d offered up time downstairs, and the soft non-judgmental way he was asking Frumpkin’s ( _Caleb’s_ ) permission to enter, and suddenly the panic drained out of him, like it was being washed away into the sea.

 _Yes,_ he thought to Frumpkin, _alright, let him in._ The tension didn’t leave him, keeping him held there, awkward and shaking slightly beside the bed, but the sheer rush of adrenaline had melted away, and when Caduceus’s head poked around the doorframe, it was almost a relief, seeing the soft curve of a smile stretch into an expression of something that might have been wide-eyed wonderment.

“Wow,” Caduceus said. He let himself into the room, closing the door behind him, and he leaned back against it, taking a moment to look Caleb over. “You look _great_.”

“I.” Caleb had lost all his words. He looked down at himself, let a hand brush over the skirt of the dress, thankful that it was full enough to hide the beginnings of his arousal. His eyes darted back up to Caduceus. “Thank you?”

“I mean, really. This is…” Caduceus took a step toward him, then paused. He settled himself onto his own bed by the door instead, folding his legs under him, and looking up at Caleb intently. “What do _you_ think?” he asked.

“I. I think.” Caleb’s voice shook slightly. “I think Jester made a good choice,” he said finally, and Caduceus’s face broke out into a grin.

“She did, didn’t she? It suits you.” He looked Caleb up and down. “Haven’t seen you in many colors before, but this is a good one.” He planted his hands on his legs. “Well.” He leaned over to reach onto the floor for his pack. “Don’t let me keep you from – “ he waved a hand “ – whatever else you needed to do tonight. I think there was a spell you were going to copy?”

“Oh.” Caleb blinked, his mind still fuzzy from processing Caduceus’s admiration. “I. Yes. There was.”

Caduceus nodded, rifling into his pack. “Good. Great. I’m just going to do some ritual stuff over here, don’t mind me.”

Caleb felt unbalanced, adrift. The rush of wearing the dress was starting to drain away, suddenly fading into something more…comfortable. Easy. Almost soothing, as he watched Caduceus settle into his work beside him. His fingers were still shaking as he drew the scroll and his paper and ink from his bag, but as he curled up on the bed and began to work, the extremity of his emotions started to calm, the careful work lulling him into security.

He looked up a few times to find Caduceus’s eyes on him, and each time it felt a little less like an intrusion, and a little more like…something was building. Simmering. He worked slowly, methodically, and when he finally rolled up the finished scroll, satisfied, he turned to find Caduceus stretched out on the other bed, blinking up at him sleepily.

“Oh.” Caleb felt a rush of shame. “I apologize,” he said. “You could have turned out the light if you were tired.”

“’m not,” Caduceus said in a low rumble that didn’t sound quite like the truth, but he propped himself up on an arm. “I was watching.”

“Watching,” Caleb repeated, and looked down at himself. “Me?” 

He hadn’t forgotten the dress, but the sight of it like this, just a part of his nightly routine, folded neatly over his lap as he worked, was strangely comforting, and when he looked up to find Caduceus’s eyes still on him, they felt the same way. Odd, unfamiliar, but not unwelcome. Even a bit exciting.

“Mmhm.” Caduceus’s expression was intent. “You like it. Looking like this.”

Caleb smoothed a hand over it. “I. Yes.” He felt a flare of uncertainty at not knowing where this was leading, so he said almost challengingly, “Do you?”

“Like you like this? Or like wearing dresses? Yes.” Caduceus answered before Caleb could clarify. “Both. I don’t really…clothes are clothes, you know? I had sisters. We all wore what was around. It wasn’t…” he shrugged. “Clothes aren’t really a thing, for me.” His eyes narrowed a little at Caleb. “I think they are for you. And for what it’s worth, you look…” he shrugged, continuing like it was as casual as the rest of his words, “incredible.”

Caleb swallowed. “ _Danke_ ,” he muttered under his breath, feeling his face heat up.

“I interrupted you before,” Caduceus said, and Caleb felt the flush of pleasure turn to one of shame. “And that probably wasn’t fair of me. I'm sorry about that.”

“I don’t – “ Caleb said. “You didn’t – “

“There was kind of a part of me that wanted to see…if you’d let me in. And then you did, and I realized I didn’t know how to…” Caduceus trailed off. “Anyway, I’m sorry if I made you uncomfortable.”

“You didn’t.” The words escaped Caleb before he really had a chance to consider them, but once they had left him, he realized they were true. The situation had been fraught, but only because of everything roiling inside of Caleb himself. Caduceus had been… “You – “ his voice tripped over the words. “You made me comfortable.”

Caduceus’s face lit up, beautiful in the low light. “Oh,” he said. “Oh, good. That’s what I like to do. Anyway, if you wanted to…uh.” He waved a hand at Caleb. “Y’know, finish what you were up to, I could sure use a nice long soak in the tub, if you’d like me out of here for a while.”

Caleb felt like his entire body was going to combust with the hot combination of shame and unexpected _want_ that surged through it. “I.” He swallowed. “I wouldn’t like that, no.”

“Ah.” Caduceus nodded. “Sure. Well, sorry again if I…y’know. Ruined anything for you.”

Caleb swallowed, taking a second to search for the words he wanted. “No, you misunderstand. I…” his voice caught in his throat. “I would like very much to…” He touched the dress over his leg, feeling like he was sending himself directly over a cliff with his next words, but making himself say them anyway. “I would like to finish what I was doing. And I would not like you to leave.”

Caduceus’s eyes snapped up to his. “Yeah?” he asked, looking faintly stunned. “Oh, wow, that’s. Yeah, okay. That’s great. That’s…I’d like that.” He sat up, suddenly looking very awake, and swung his long legs over the side of his bed, resting on them as he leaned toward Caleb. “Would you like…um. What would you like?”

Caleb considered. Caduceus’s eyes on him were intoxicating, and there was part of him that wanted to indulge in that, to touch himself through the soft fabric of the dress and watch Caduceus watching him. But then his mind was whirling back to his thoughts as he stood in front of the mirror before, closing his eyes and imagining being able to feel someone else’s hands on him (warm, soft, broad hands), and he let out a shuddering breath before admitting all in a rush, “I’d like you to touch me. If you would.”

“I – uh, yeah. Yeah, I would,” Caduceus agreed, and Caleb felt the smallest of smiles twist his lips at the eagerness creeping into his voice. “You want me…over there? Or…”

Caleb hesitated, but he was in this now, he was doing this, so instead of answering or looking at Caduceus, he rolled over, standing on the opposite side of the bed, and he crossed to the mirror on shaky legs. “Before,” he said, looking into the mirror at his reflection, the dress more rumpled than it had been before, but looking more settled against his body, “before you came in. I was…I was here. Looking. And…” he let a hand trace up the skirt, tugging at the fabric, his fingers trailing along the soft skin of his leg underneath. He heard Caduceus draw in a sharp breath behind him, and he let his eyes drift shut, the sensations heightened now with the knowledge that he wasn’t alone. He touched himself lightly, teasingly, and heard the shift of Caduceus moving across the room, felt his warmth settling in behind him.

“Wow, that’s…” Caduceus’s voice was a low rumble, his breath a tickle against Caleb’s neck that made him shiver. “That looks nice.”

Caleb didn’t know what he was expecting, but it wasn’t for Caduceus’s hand to rest over his own, to trace the same path, following Caleb’s lead so carefully, so methodically. Eventually, his fingers found their way to the soft dress and Caleb’s skin on their own, and Caleb let his hands drop to his sides, letting some of his weight sag back against Caduceus, feeling so warm, so supported, his nerve endings starting to light up with the sensations of Caduceus’s hands touching him all over, arousal gathering in him.

“Could I…” Caduceus asked finally, his fingers drifting up the skin of Caleb’s thigh, and Caleb let out a strangled moan, his head dropping back against Caduceus’s shoulder.

“Please,” he breathed out, and his whole body shuddered as one of Caduceus’s hands wrapped around him, the other gathering the fabric of the dress, bunching it up against his waist. There was still enough of it trailing downwards that it brushed tantalizingly against the tip of his cock, and Caleb felt like he might black out from sheer _need_.

“Hey.” He felt Caduceus’s voice against his back more than hearing it, and he tore his eyes open to meet Caduceus’s in the mirror. “You good?”

“I’m – “ Caleb felt like he couldn’t get enough breath to form the words. His eyes dropped to the sight of Caduceus’s hand wrapped around him, the skirt of the dress framing the image almost obscenely. “I don’t know,” he managed, “that I have ever been better.”

Caduceus beamed. “Good,” he said, “that’s good,” and Caleb was nowhere near having the presence of mind at this moment to examine the way that the words made a soft rush of warmth run through him. He watched Caduceus press a light kiss against the side of his head in the mirror, then closed his eyes again, letting the solid warmth of Caduceus’s grip and the tantalizing brush of fabric overwhelm him.

“I – “ he gasped out finally, his hips jerking forward into Caduceus’s touch. “Caduceus, I – “

“Yeah,” Caduceus said against his ear, voice low and pleased, and Caleb hadn’t realized that he’d been waiting for that affirmation, but as soon as he had it, he was falling apart, his hips thrusting erratically into Caduceus’s hand, body collapsing bonelessly against him as the pleasure tore through him. “Hey,” Caduceus said, his other hand dropping the dress so his arm could go around Caleb more supportively, “Yeah. I’ve got you.”

Caleb tilted his head, pressing his face into the velvety softness of Caduceus’s neck as he let out a breath that felt like a sob, and he felt both of Caduceus’s arms curl around him, gathering him close. They stayed like that for a long time, until Caleb lifted his head just enough to press a kiss to Caduceus’s skin. 

Caduceus let out a rumble of approval. “What would you say to getting off our feet?” he asked, his voice low, and Caleb nodded, letting Caduceus lead him on stumbling feet back toward his bed. He sank into it gratefully, not letting go of Caduceus, dragging him down onto the sheets with him.

He sprawled out on his back, staring up at the ceiling and letting one of his hands idly stroke over the soft almost-fur of Caduceus’s arm. He knew the thoughts would come tumbling back in soon, but for now he felt pleasantly blank, and when he let his head to the side, he could see Caduceus watching him with a fond smile.

“I liked that,” Caduceus said, and Caleb felt a laugh leave him without any warning.

“ _Ja_ ,” he agreed. “The same for me.”

“Good.” Caduceus lifted the arm that Caleb wasn’t holding, and brushed his knuckles over the skirt of the dress.

Caleb looked down at it ruefully. “I’m going to need to wash Jester’s dress.”

“It’s your dress,” Caduceus said. 

Caleb felt his cheeks get pleasantly warm at that. He knew Caduceus was right, that Jester would never want it back, that she was as generous with her possessions as she was with everything else (except her healing), and that it was _his_. “It is, isn’t it?” He curled onto his side, looking Caduceus over. He looked pleased and relaxed, like _he_ was the one who had just been elaborately taken apart in front of the mirror. “Could I…?” Caleb asked, feeling oddly hesitant about it, even after everything. “I mean, would you like…?”

“Oh, not right now,” Caduceus said easily. A smile tugged at his lips. “Although I did mean it, about needing a wash.” There was a twinkle in his eye as he looked at Caleb. “Interested in joining me?”

“Yes.” The word was out of his mouth nearly before Caduceus finished speaking, and Caduceus beamed.

“Great,” he said. He yawned and stretched, and his arms reached out to pull Caleb close to him. “In a minute,” he said. His hands drifted over Caleb’s back, solid and grounding through the dress. “I don’t think you need to get out of this just yet.”

“No,” Caleb agreed. “I don’t think I'd like to,” and he let his head fall to Caduceus’s chest, letting himself lay there for just a moment more, peaceful and guarded by his alarm at the door, his cat in the hallway, and the strong gentle arms around him.


End file.
